Jack Black was a late 19th century hobo, living out the dying age of the Wild West. He wrote You Can't Win, a memoir or sketched autobiography describing his days on the road and life as an honourable outlaw (to live outside the law you must be honest).
Jack Black is an essentially anonymous figure (even his actual name is uncertain) who is recognised through association with William S. Burroughs. His philosophy on life was influential to Burroughs, who associated with similar characters in his early adulthood and mirrored the style of "You Can't Win" with his first published book, "Junkie".
Jack Black died sometime in the early 20th century, possibly commiting suicide.
JackBlack was a late 19th century/early 20th century hobo, living out the dying age of the Wild West.
Black's book was written as an anti-crime book urging criminals to go straight but is also his statement of belief in the futility of prisons and the criminal justice system, hence the title of the book.
JackBlack was writing from experience, having had plenty of experience in petty crime himself for which he did time in jail.
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